The Official SaaStr Podcast: SaaS | Founders | Investors

Kyle Porter is the Founder & CEO @ Salesloft, the leading sales engagement platform delivering a better sales experience. To date, Salesloft have raised over $75m in funding from some of the best in the business including Emergence, Insight Venture Partners, Techstars and even LinkedIn. As for Kyle, he has led the team from 4 employees in 2014 to over 320 today where they have also been awarded Atlanta's No 1 best place to work. Prior to founding Salesloft, Kyle was the Founder @ B2B camp, a conference focused on B2B revenue generating professionals. Before that he was Vice President of Marketing @ NanoLumens.

In Today's Episode We Discuss:

• How Kyle made his way into the world of SaaS and came to found Salesloft?
• Kyle made the decision to pivot the product when it was at $7m in ARR, what was the thinking behind that? How does Kyle think about pivots more broadly? How does one know when it is truly not working? How long did it take Kyle to get the core Salesloft product to $1m in ARR?
• With the pivot, what were Kyle's core learnings on migrating from a prior product and platform to a new one? What were his big lessons on seeing the change in buyer persona? What does Kyle mean when he says "selling is hard but buying is even harder"?
• Does Kyle agree with many CEO's the most important role of the CEO is "management upscaling"? What elements does he find most challenging? What have been Kyle's big lessons in the building out of his exec team? What is the fundamental element for a successful exec team to function?
• Salesloft is in an immensely competitive space, what would Kyle's advice be in standing out in an intensely competitive space? Where do many go wrong? What are the pros and cons of being in Atlanta and not SF? What advice would Kyle give to founders operating their HQs external to the core hubs?

Kyle's 60 Second SaaStr

Is it important to have early champions? How does one get them?

How has having kids changed your perspective on work?

Tell me a moment in your life that has served as an inflection point and changed the way you think?

When I say success in SaaS who is the embodiment of this to you?

What does Kyle know now that he wishes he had known at the beginning?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin Harry Stebbings SaaStr Kyle Porter

Ed Sim is the Founder & General Partner @ Boldstart Ventures, one of the leading players in early stage SaaS investing. Their MO, to be a first check VC for enterprise founders and they have backed the likes of GoToMeeting (acq by Citrix), LivePerson (IPO, NASDAQ), Divide (acq by Google), Kustomer, Snyk and BigID just to name a few. Ed is also a cofounder of MState, a growth lab for enterprise blockchain in partnership with IBM. Ed is also a board director/observer of Kustomer, Hypr Biometric, Snyk, BigID, Fortress IQ, Wallaroo Labs and Manifold. If that wasn't enough, Ed is also the writer behind BeyondVC, a must read blog in the world of SaaS.

In Today's Episode You Will Learn:

• How Ed made his way into the world of VC from one very meaningful high school lecture that changed his life and career path?
• What does Ed mean when he says "founders should not sell their product to enterprise in the early days". Starting from the ground up, what can founders do to begin that relationship building process with enterprise buyers and CIOs? What can a startup do to establish that trust in the mind of large buyers? How much of a role does VC backing provide in comforting enterprise buyers?
• What would Ed advise founders contemplating the debate of going SMB up to enterprise or enterprise to SMB? What role should product play in this decision-making process? What are the leading indicators in testing the product that founders should observe for and guide their direction? Where does Ed most often see founders make mistakes here?
• How does Ed think about discounting? Would he agree with a previous guest that "discounting is now table stakes"? Rather than the financial element, what does Ed believe the founder should really be looking to get from the buyer in terms of commitment? How does Ed approach and assess pilots? To what extent should they be free or paid? What can be done to set the benchmarks for success and ensure closing?

Ed's 60 Second SaaStr

1. What does Ed know now that he wishes he had known in the beginning?
2. Quality or quantity of logos?
3. What would Ed most like to change in the world of SaaS?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Ed Sim

Craig Walker is the Founder & CEO @ Dialpad, the startup that provides a business phone system for the modern workplace. To date, Craig has raised over $120m in VC funding with Dialpad from some of the best in the business including Iconiq, Andreesen Horowitz, Google Ventures, Felicis and Bill Marris's Section 32. Prior to Dialpad, Craig was an EiR @ Google Ventures and founded and product managed Google Voice. Before that Craig founded Grand Central Communications, a personal communications startup that was acquired by Google. Finally prior to that, Craig enjoyed roles in the world of VC as General Partner @ Sterling Payot Capital and Founder & Senior Director of Yahoo Voice.

In Today's Episode You Will Learn:

• How Craig made his way into the world of SaaS following time as both a GP in the world of venture and then as the creator of what would become Google Voice?
• Why does Craig think go-to-market is the most challenging element of being a CEO? How does Craig think about when is the right time to go large on go-to-market? Where does Craig believe most founders make mistakes here?
• How does Craig look to balance aggressive scaling of team with the maintaining of early company culture? What are the foundations to doing this successfully? How does Craig approach the element of hiring external talent vs promotion from within? How does Craig think about managing the internal discontent if hiring an external candidate?
• How does Craig assess the effectiveness of trials in attracting large enterprises? What are the parameters that must be set for a trial, before it is agreed? What must founders learn to say no to when it comes to trials? How does Craig approach discounting? Why does Craig argue if your client asks for aggressive discounts, you have not explained your core USPs successfully?

Craig's 60 Second SaaStr

1. What does Craig knows now that he wishes he had known at the beginning?
2. When I say success in SaaS, who does Craig first think to and why?
3. Quality or quantity of logos and why?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Craig Walker

Fouad ElNaggar is the Founder & CEO @ Sapho, the only employee experience portal designed for the digital workforce. To date, Ray has raised over $27m in funding with Sapho from some real favourites of ours including Ray @ Caffeinated, Felicis, Uncork, Bloomberg Beta, Clark Landry and Howard Lindzon @ Social Leverage, just to name a few. Prior to founding Sapho, Fouad was the Chief Strategy Officer at CBS Interactive overseeing strategy, operations, partnerships, and M&A. At CBSi, Fouad structured deals with partners such as Yahoo, IAC, and Twitch and acquired premium brands such as TV Guide and Giant Bomb. Prior to CBSi, Fouad was a VC at Redpoint Ventures overseeing the firm's LA office and helping establish a dedicated fund in Brazil. Fouad has previously founded three venture-backed companies – Marketing Technology Solutions (acquired), Liquid Light (acquired), and Hark.

In Today's Episode You Will Learn:

• How Fouad made his way from the world of VC to the world of CBS and media to founding SaaS companies being a serial SaaS founder with his 4th company, Sapho?
• What does Fouad mean when he says the role of the CEO is to be an "inspirational asshole"? Why is this role so crucial and how is it embodied both in the approach to inspiring a team and driving goals and decision-making? How does Fouad think about structuring decision-making internally? Where do so many go wrong in implementing a decision-making process?
• Why is Fouad a believer that "it is about coaching and promoting rather than signal hiring"? What does Fouad really interpret as signal hiring? When does signal hiring work well? How does Fouad determine when a stretch VP is a stretch too far? What are the leading indicators? Does Fouad agree with Mariam Naficy that rotation of function is key to internal upscaling?
• What does Fouad believe are the 2 fundamental benefits of "being old" in SaaS? How would Fouad respond to the suggestion that the rate of decay on experience has never been greater with Moore's law effect on technology? Applied to hiring, how does Fouad think about the decision to hire a jack of all trades vs a specialist? When is the time to make the transition?

Fouad's 60 Second SaaStr

1. What does Fouad know now that he wishes he had known at the beginning?
2. A moment in Fouad's business life that changed the way he thinks?
3. What would Fouad most like to change in the world of SaaS today?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Fouad ElNaggar

Christoph Janz is the Managing Partner @ Point Nine Capital, one of Europe's leading early stage funds with a portfolio that includes the likes of ZenDesk, Algolia, Delivery Hero, Revolut, Contentful and many more incredible companies. Before that, he co-founded two Internet startups (DealPilot.com in 1997 and Pageflakes in 2005). In 2008 he became an angel investor and discovered Zendesk, Clio, FreeAgent – and his love for SaaS. Christoph is also the writer of the phenomenal blog, The Angel VC, a must read for me.

In Today's Episode You Will Learn:

• How Christoph made his way from serial founder to angel in ZenDesk to today, founding one of Europe's most successful early stage funds in the form of Point Nine Capital?
• Product market fit is one of the most used words in the industry, so wtf really is product market fit? What does product market fit look like in terms of metrics across the core disciplines: MRR, churn and conversion from free to paid?
• What is the hailed question that all Series A and B investors want to know? What does it take to make the graduation from Seed to Series A today? In terms of scaling, why does pouring fuel on the marketing fire not always equal more leads? How does Christoph view the role of outbound? Why is it such high hanging fruit? What is core to executing outbound successfully?
• Point Nine did a comprehensive assessment of how founders view the fundraising process, what were the biggest elements founders dislike about the process? From now on, what is the thinking behind the strategy that Point Nine will always do their pro-rata in the Series A? How does this affect reserve allocation?

Christoph's 60 Second SaaStr

1. What does Christoph know now that he wishes he had known in the beginning?
2. What does it take for European founders to make it big in the US?
3. Most common mistakes CEOs make in the scaling process?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Christoph Janz

Tom Bogan is the CEO of Adaptive Insights, the company that proves a new generation of business planning software for finance and beyond. Prior to their reported $1.55Bn acquisition to WorkDay, Adaptive Insights raised over $175m in VC funding from the likes of Bessemer, Salesforce Ventures, Norwest Venture Partners and many more incredible investors. Prior to Adaptive Insights, Tom was a partner at Greylock Partners where he focused on enterprise software investments. He was also president and COO at Rational Software until its acquisition by IBM. Before Rational, Tom served as CEO at Avatar Technologies and Pacific Data. He began his career as a financial officer in both public and private companies, serving as CFO at SQA and Orange Nassau, Inc., as well as vice president of finance at SCA Services.

In Today's Episode You Will Learn:

• How Tom made his way into the world of SaaS, came to be a Partner with Greylock and then made the move back into operations with Adaptive Insights?
• Elad Gil has previously said the role of CEO is to "find product market fit, ensure the company does not run out of money and ensure the team does not implode", how does Tom define his role as CEO of a $100m+ SaaS company? How does the role of CEo fundamentally change over time? What aspect of the role does Tom find most challenging?
• What core role of CEO is constant throughout the lifecycle of the company? From seeing many of the world's best SaaS CEOs, what are the commonalities in how the very best CEOs hire the very best execs? How does Tom think about the debate of hiring externally or promoting from within? How does Tom look to reduce internal discontent when hiring externally rather than promoting?
• At $100m Jyoti Bansal said on the show, this stage is about "creating and sustaining operational efficiency". What have been Tom's biggest learnings on the creation and maintenance of operational efficiency? What has worked? What has not worked? How does Tom think about internal asset allocation?
• Why does Tom believe that ultimately, ARR growth is the metric to rule them all? How does Tom think about and prioritise the metric stack in SaaS? How does he approach payback period vs CAC/LTV? In terms of services components of businesses, does Tom believe these should be baked into the CAC? What should the financial targets be for these services businesses?

Tom's 60 Second SaaStr

1. What does Tom know now that he wishes he had known at the beginning?
2. Tom's favourite business reading material and why?
3. What would Tom most like to change in the world of SaaS today?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Jonah Goodhart is the CEO @ Moat, the SaaS analytics and intelligence company focused on transforming brand advertising online. Prior to their acquisition by Oracle for a reported $850m Moat raised over $67m in VC funding from the likes of Insight Venture Partners, Founders Fund, Mayfield, Founder Collective, SV Angel and more incredible names. Prior to founding Moat, Jonah was the founding investor and board member at Right Media, acquired by Yahoo for a reported $680m. Jonah was also the founding partner of WGI Group and co-founder of Billions.org. If all of that was not enough, Jonah is also an angel investor including the likes of adroll, Namely and fitmob all in his personal portfolio.

In Today's Episode You Will Learn:

• How Jonah made his way into SaaS with is founding investor role in Right Media? How did experiencing both bubbles change the way Jonah thinks about operations today?
• How does Jonah fundamentally define "North Star"? How plastic and flexible does Jonah believe a North Star should be? What was a time where Jonah's decision was guided in a certain direction by his strong North Star?
• Why does Jonah believe that in B2B your roadmap is given to you by your customers? What can founders do to clearly and quickly determine what their customers want from their conversations with them? What questions are crucial to ask? What response suggests real intent to buy from them? How does one prevent this from falling into heavy customisation?
• How does Jonah approach the element of "brand" in the world of B2B today? What does Jonah believe is the secret to brand? How does this affect how Jonah both onboards, trains and engages with new and existing employees? Was brand core to Moat being able to sell to enterprise so successfully in the early days?

Jonah's 60 Second SaaStr

1. What does Jonah know now that he wishes he had known at the beginning?
2. Quality or quantity of logos in the early days?
3. How important is it for SaaS founders to be involved in the process?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Jonah Goodhart

Sam Blond is Chief Sales Officer @ Brex, the startup that provides corporate cards for startups. To date they have raised over $57m in funding from the likes of Y Combinator, Peter Thiel, Max Levchin, Yuri Milner, Elad Gil and many more incredible names. Prior to Brex, Sam Was Chief Revenue Officer at Rainforest QA. Before Rainforest, Sam saw firsthand the hypergrowth scaling of Zenefits as VP of Sales where he saw the company grow from 18 employees and $1m in ARR to over 1,800 employees and over $70m in ARR. Sam got his start in the SaaS industry with Jason Lemkin @ Echosign as Director of Sales.

In Today's Episode You Will Learn:

• How Sam made his way into the world of sales and came to join Jason Lemkin with his first role in sales at Echosign?
• Why does Sam believe that more sales reps does not always equal more revenue? What are the benchmarks that suggest founders really need to add to their sales team? Does Sam agree Founders should be selling up to $1m in ARR?
• How does Sam assess who is the best person to hire for the role? What have been Sam's lessons on what it fundamentally takes to attract the best talent? In the early days how does Sam think about both role allocation and whether to hire the young jack of all trades vs the more senior executive?
• Why does Sam believe that founders need to spend more time on top of funnel? Why does Sam believe that not all opportunities are created equal? How does Sam think about the right structure and time it should take to pass from lead to MQL to SAL to opportunity to deal? Where does this most commonly breakdown?
• Why does Sam believe the key to success in SaaS sales teams is "urgency"? Literally, how can reps instil a sense of urgency in their current pipeline? Why does Sam disagree with the conventional wisdom and say discounting is a great tool? How does Sam determine the right level of discount to give? How does Sam assess pilots as an alternative approach to getting leads over the line?

Sam's 60 Second SaaStr

1. What does Sam know now that he wishes he had known at the beginning?
2. Quality or quantity of logos in the early days?
3. Sales rep productivity, what does Sam believe is good?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Sam Blond

Eoghan McCabe is the Co-Founder & CEO @ Intercom, one of the fastest growing saas companies of the day providing a new and better way to acquire, engage and retain customers. Due to their phenomenal growth they have raised over $240m in funding from some of the best in the world including Kleiner Perkins, Social Capital, Bessemer and Index, just to name a few. As for Eoghan, prior to co-founding Intercom, he founded an award-winning software design consultancy called Contrast, and co-founded Exceptional, a developer tool startup acquired in 2011 and now a part of Rackspace.

In Today's Episode You Will Learn:

• How did Eoghan come to be founder of one of the hottest growing startups in SaaS from founding a software design firm in Ireland?
• What does Eoghan believe are the core pillars for success in making the move from SME to enterprise? How does one reinvent oneself to make this transition? How has Eoghan seen te org structure and internal decision-making change with the adoption of many more enterprise clients?
• How does Eoghan determine between the decision to hire the young jack of all trades vs the much more experienced senior exec? Why does Eoghan believe you can never be too early to bring someone more senior than you onto the team? What makes Eoghan say, "we are all learning on the fly"?
• How does Eoghan look to create a culture of experimentation and accountability without the fear of failure? What must the leader do to imbue this culture? Where does Eoghan see many going wrong in trying to make this happen?
• How does Eoghan think about "transparency" with SaaS companies today? Why does he think that not only is it not healthy but also largely not possible? Instead, what is a better, more sustainable solution to transparency?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Eoghan McCabe

Steve Lucas is the CEO @ Marketo, the world leader in marketing automation for companies of any size. Prior to their IPO and eventual sale to Vista Equity partners for $1.79Bn they raised over $100m in VC funding from the likes of Battery Ventures, IVP, Mayfield and Lead Edge Capital. As for Steve, prior to joining Marketo, he served in many leadership positions at SAP, Salesforce, Microsoft, BusinessObjects, and Crystal Decisions. If that wasn't enough Steve also sits on the board of Tivo, SendGrid and The American Diabetes Society.

In Today's Episode You Will Learn:

• How did Steve make his way into the world of SaaS and come to be CEO @ Marketo?
• Why does Steve describe his experience at Salesforce to be life-changing? What were the core takeaways for Steve? How has that impacted how he operates today with Marketo? What does Steve mean when he says Marc Benioff is a "master of relevance"?
• Why does Steve believe the key to success as a CEO is accessibility? How can CEOs be both vulnerable and strong in today's SaaS world? What are the 2 different types of CEOs and how they engage with their CMOs? What do the best do? What do the worst do?
• Why does Steve believe that the "CRM" term is incomplete? How does Steve fundamentally believe the way that customers want to be engaged with has changed? How can marketers enact this level of personalisation and engagement with such large customer bases? How does the role of artificial intelligence fit into this mass scale personalisation?
• How does Steve view the broader martech landscape? Why does Steve strongly believe that we will be entering a period of consolidation in martech? How does Steve view the emergence of new categories such as ABM? How does this impact his overarching view on the next wave for martech?

Steve's 60 Second SaaStr

1. What does Steve know now that he wishes he had known when he started?
2. Management upgrade is the most important role of CEO, agree?
3. What keeps Steve up at night? How does that influence his running and operations of Marketo?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Steve Lucas